For tax purposes, you really just need to have everything aligned to the schedule E categories. 

@Daniel Tanasa $1905 per month (mortgage +interest) , taxes (around 3600 per year) and insurance (1500 per year) => so 2330$ is my PITI

Thanks again for your input, and I'll probably reach out as I get further along in the process.Hi @Edward Zachary Samperio, the regulations aren't that difficult and I'd be happy to give you a quick rundown about the density limits, hotel occupancy taxes, permitting, etc.

High taxes.

.: What is the average conversion rate for cold calling using software like PropStream, specifically targeting probate, foreclosure, or tax delinquency leads?

@Emily Gowen so as you pointed out you would not have to do a 1031 exchange on your current home to avoid the capital gains tax and coupled with what Dave Foster pointed out I think, speaking from experience you would have a high likelihood of success. 

Maintain - includes taxes and insurance?

A rent payment isn't enough to cover the DSCR payment, HELOC payment, tax, insurance, and maintenance.

He was a good guy” and his information  on buying at tax or foreclosure sales was realistic and doable. 

The area has certain advantages like shelter from regulation risk (pretty much as low as anywhere in the country if you buy in the approved STR tourist zones) and long term security (people aren't going to stop going to Orlando anytime soon).